AT71165B - Process for the preparation of anthraquinone. - Google Patents
Process for the preparation of anthraquinone.Info
- Publication number
- AT71165B AT71165B AT71165DA AT71165B AT 71165 B AT71165 B AT 71165B AT 71165D A AT71165D A AT 71165DA AT 71165 B AT71165 B AT 71165B
- Authority
- AT
- Austria
- Prior art keywords
- nitric acid
- anthraquinone
- parts
- chlorine
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title description 6
- 150000004056 anthraquinones Chemical class 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 claims description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002730 mercury Chemical class 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 241000589614 Pseudomonas stutzeri Species 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Anthrachinon.
EMI1.1
<Desc/Clms Page number 2>
Salpetersäure eingelaufen ist, tritt völlige Lösung ein. Zuc Beseitigung der im technischen Anthrazen häufig enthaltenen Verunreinigung wird filtriert. Das Filtrat wird noch 3 weitere Stunden auf 350 erwärmt. Darauf wird die Salpetersäure abgetrennt. Es werden 360 TeileSalpetersäure von 15'60 Be wiedergewonnen. Zum Nitrobenzolteil wird eine Lösung von 5 Teilen Quecksilber in 65 Teilen Salpetersäure 40"Be zugefügt und beispielsweise in 25 Minuten auf 1050 erhitzt. Die Temperatur steigt noch rasch auf 1200, darauf wird bei etwa 1100 noch etwa 10 Minuten Chlor eingeleitet, um in geringer Menge gebildete organische Quecksilberverbindungen zu entfernen.
Nach dem Erkalten werden die abgeschiedenen Anthrachinonkristalle abgesaugt, mit Nitrobenzol und Petroläther ausgewaschen und getrocknet.
Beispiel 3 : 117 Teile Anthrazen von 850/0 Reingehalt werden in 300 Teilen Nitrobenzol suspendiert. Man lässt in 3 Stunden bei 300 eine Lösung von 15 Teilen Quecksilber in 460 Teilen piger Salpetersäure einfliessen und rührt noch 3 Stunden bei 350 und filtriert, wenn nötig.
Darauf wird die Salpetersäure abgetrennt. In das Nitrobenzolfiltrat wird unter Rühren ein kräftiger Chlorstrom eingeleitet und in etwa 20 Minuten auf 1000 erwärmt.
Die Temperatur steigt dann unter fortwährendem Chloreinleiten auf 110 bis 1200'das Chloreinleiten und Erwärmen wird noch einige Zeit fortgesetzt. Darauf heisst man abkühlen.
Die Anthrachinonkristalle werden abgesaugt, mit Nitrobenzol und Benzin gewaschen und getrocknet.
In analoger Weise kann man statt des Chlors Stickstoffdioxyd, Stickstofftrioxyd oder Gemische beider verwenden. Auch andere leicht sauerstoffabgebende Substanzen, wie Mangansuperoxyd können Verwendung finden. Man kann auch in der zweiten Phase Queck- silbersalze noch besonders zusetzen.
PATENT-ANSPRÜCHE :
1. Verfahren zur Darstellung von Anthrachinon aus Anthrazen mit Hilfe von Salpetersäure, dadurch gekennzeichnet, dass man Anthrazen bei Gegenwart eines geeigneten Lösungs- oder Suspensionsmittels erst bei unter 600 liegenden Temperaturen mit Salpetersäure be- handelt und die Umsetzung des gebildeten Zwischenproduktes zu Anthrachinon mit Salpeter- säure bei höheren, über 600 liegenden Temperaturen vornimmt.
<Desc / Clms Page number 1>
Process for the preparation of anthraquinone.
EMI1.1
<Desc / Clms Page number 2>
If nitric acid has run in, it will dissolve completely. Zuc Removal of the impurities often contained in technical anthracene is filtered. The filtrate is heated to 350 for a further 3 hours. The nitric acid is then separated off. 360 parts of nitric acid of 15'60 Be are recovered. A solution of 5 parts of mercury in 65 parts of nitric acid 40 "Be is added to the nitrobenzene part and heated to 1050 in 25 minutes, for example. The temperature rises rapidly to 1200, then at about 1100 chlorine is passed in for about 10 minutes to reduce the amount to remove organic mercury compounds formed.
After cooling, the deposited anthraquinone crystals are filtered off with suction, washed out with nitrobenzene and petroleum ether and dried.
Example 3: 117 parts of anthracene of 850/0 pure content are suspended in 300 parts of nitrobenzene. A solution of 15 parts of mercury in 460 parts of pigerous nitric acid is allowed to flow in over 3 hours at 300 and stirred for 3 hours at 350 and filtered if necessary.
The nitric acid is then separated off. A vigorous stream of chlorine is passed into the nitrobenzene filtrate with stirring and heated to 1000 in about 20 minutes.
The temperature then rises to 110 to 1200 'with the continuous introduction of chlorine. The introduction of chlorine and heating is continued for some time. Then you have to cool down.
The anthraquinone crystals are filtered off with suction, washed with nitrobenzene and gasoline and dried.
In an analogous manner, nitrogen dioxide, nitrogen trioxide or mixtures of both can be used instead of chlorine. Other easily oxygen-releasing substances, such as manganese peroxide, can also be used. Mercury salts can also be added in the second phase.
PATENT CLAIMS:
1. A process for the preparation of anthraquinone from anthracene with the help of nitric acid, characterized in that anthracene is only treated with nitric acid at temperatures below 600 in the presence of a suitable solvent or suspension medium and the conversion of the intermediate product formed into anthraquinone with nitric acid acid at higher temperatures above 600.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE71165X | 1913-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT71165B true AT71165B (en) | 1916-02-10 |
Family
ID=5635697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT71165D AT71165B (en) | 1913-06-06 | 1914-05-16 | Process for the preparation of anthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT71165B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1091554B (en) * | 1956-03-28 | 1960-10-27 | Koppers Co Inc | Process for the production of anthraquinone by oxidation of anthracene |
-
1914
- 1914-05-16 AT AT71165D patent/AT71165B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1091554B (en) * | 1956-03-28 | 1960-10-27 | Koppers Co Inc | Process for the production of anthraquinone by oxidation of anthracene |
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